We tend to remember Indiana Jones as a Nazi-fighting, world-saving, rough-and-tumble adventurer, not as a Professor of Archeology. We tend to remember Erin Brockovich as a feisty, community-minded legal aid who held corporations accountable, not as a single mom. And we tend to remember Sidney Dean from White Men Can’t Jump as a fast-talking, flashy streetball player with a silly hat and too high of a dribble, not as a renovation contractor. Why? Because these characters are known for their successful side hustles, not their full-time role. When executed properly, side-hustles can advance your career. Even if it doesn’t transform you into a world-renowned adventurer, a side hustle can teach you new skills and introduce you to new communities. Here are six professional lessons from six movie side hustles.

What are side hustles?

Being a fairly entrepreneurial concept, we have chosen the Entrepreneur magazine definition of “side hustle”:

“A side hustle is a way to make some extra cash that allows you flexibility to pursue what you’re most interested in. It can also be your true passion – a chance to delve into fashion, travel or whatever it is you care about the most without quitting your day job.”

Here’s how this idea comes to life through the lens of pop culture and our blog’s six competencies.

Leadership

The Movie

Erin Brockovich, which is about a legal aid who almost single-handedly takes down an evil corporation.

The Side Hustle

Being a legal clerk. Specifically, taking a gig as a legal clerk while being a full-time mom and then being so great at the work that capitalism takes a hit.

The Lesson

Erin Brockovich probably knew that she was a badass, caring human being, but she might not have realized her abilities as a community organizer and activist had she not explored the legal aid gig. Side hustles cultivate new skills and unlock our potential by opening us up to new experiences. They can also help us make a personal connection to our values and leadership style.

Learning & Thinking

The Movie

Raiders of the Lost Ark (The Indiana Jones franchise), which is about a world-saving-adventurer with a complicated ethical code (Nazis = bad, but taking artifacts from indigenous communities = okay).

The Side Hustle

Adventure. Specifically, leaving what we assume is a tenure-track professorship at a prestigious university to bring the classroom to the community with car chases, daring escapes, puzzle-solving, and romantic escapades.

The Lesson

The best kind of academia blends ideas from books and journals with hands-on experience in the field. Your side hustle should unlock different aspects of your potential from your day job as well as test your ideas and expertise in the real world, which is why Indy’s university administrators cultivate his interests through a side gig. Grave robbing, for the record, isn’t a suitable source of extra income in our opinion. Returning a magical stone to a rural community because you learned a valuable life lesson is a much better hustle.

Collaboration

The Movie

White Men Can’t Jump, which is about realizing personal potential through somewhat volatile and always hilarious basketball partnerships.

The Side Hustle

Basketball. Specifically, hustling street basketball and how it achieves racial harmony; albeit imperfectly. Also, kinda Jeopardy

The Lesson

“Sometimes when you win, you actually lose. And sometimes when you lose, you actually win. And sometimes when you win or lose, you actually tie.” This is the heavy philosophical quip from Gloria (Rosie Perez) about the nuances of victory. Billy Hoyle (Woody Harrelson) loses his romantic partner, Gloria, because he chose to invest her Jeopardy money in a pickup game, breaking her trust. Billy gains a friend and collaborator in Sidney Dean (Wesley Snipes), though. Billy’s side gig, as it turns out, represents his true passion and probably inspires more career satisfaction than living a conventional life with a less-risky day job.

Creativity

The Movie

Shakespeare in Love, which is about how a young William Shakespeare’s (Joseph Fiennes) affection for Viola De Lesseps (Gwenyth Paltrow), “the daughter of a wealthy merchant” who is “forbidden to perform on stage because she is a woman”, inspires the famous play “Romeo and Juliet”.

The Side Hustle

Acting. Specifically, De Lesseps’s shattering of gender norms by performing alongside William Shakespeare and bringing down the house for Queens and commoners alike!

The Lesson

A passion-project-side-hustle, which is how Kurt and I describe our awesome blog, not only feeds your soul, but it can also expose you to new environments and networks. The collision of classes and genders showcases how De Lesseps’s secret gig as an actor changed her perspective and, more importantly, those of the men with whom she shared the stage.

Communication

The Movie

Good Will Hunting, which is the story of Will Hunting (Matt Damon), an unrecognized genius with a troubled past. He seeks to defeat his personal demons and unlock a bright future of possibilities with the help of a physiatrist played by Robin Williams.

The Side Hustle

Being a genius. Specifically, mysteriously solving complex mathematical problems on MIT hallway chalkboards and outsmarting smug Harvard undergraduate students.

The Lesson

Will is an angry young man who seeks to express himself through his intelligence because he’s fearful of communicating his true needs and desires in his day to day work. If you look at side hustles as an additional channel to understand yourself, be vulnerable and communicate what you’re passionate about (like Will), you’ll be in great shape. We learn when we get more comfortable with being uncomfortable.

Adaptability

The Movie

Batman Begins tells the story of billionaire Bruce Wayne, who after the murder of his parents, trains as a ninja and then becomes the Batman, a vigilante who keeps the streets of Gotham City safe and gives hope to its citizens.

The Side Hustle

Crime fighting. Specifically, crime-fighting while dressed as a giant bat and inspired by ninjas.

The Lesson

Bruce Wayne’s side hustle gets off to a rocky start. His costume doesn’t inspire fear in the hearts of his enemies, he’s constantly getting hurt as he hurtles himself from one balcony to the next, and he doesn’t have the equipment he needs to accomplish his mission. Rather than give up, he adapts. Gradually he improves his approach, tech and builds allies such as Luscious Fox and Jim Gordon to evolve his side hustle into his calling. This tenacity and willingness to change his side hustle should be an inspiration to any of us. Spending time, money and energy on the Batman side hustle arguably pays off as the best of Bruce Wayne’s diverse investment portfolio.

Other movies and lessons

  • 8 Mile, which is the semi-fictionalized biopic of Eminem teaches us that factory workers with a penchant for rap battle side hustles can find their voice and success on their own terms.
  • Every superhero franchise involves a side hustle in service of the greater good; my favourite example is Thor, whose day job is “God of Thunder” and “Heir to Asgard” and whose side hustle is “avenging” and reveals what it takes to collaborate with complicated personalities, like a Hulk.
  • Sister Act, which is about a lounge singer named Deloris who is placed in witness protection as a nun and then side hustles herself into a choir-leadership role that teaches her a lot about communicating through song.
  • Hollywood Homicide, which is, I think, an underrated movie where two cops are closing a case while one is closing a real estate deal and the other is winning an audition; we all probably learn about time management.
  • Fight Club, which is, like, a side hustle within a side hustle because Tyler Durden works as an insurance adjuster, I think, and has an alter ego who side hustles as a super-disruptive underground fighter who grows the community into a global anarchist/liberation movement.

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